BICYCLIC NITROGEN-CONTAINING COMPOUNDS AS MUSCARINIC M1 RECEPTOR AGONISTS Russian patent published in 2019 - IPC C07D401/14 C07D401/04 C07D405/14 C07D409/14 C07D413/14 C07D417/14 C07D491/107 A61K31/4545 A61P25/00 

FIELD: chemistry.

SUBSTANCE: invention relates to a compound of formula (1b)

or pharmaceutically acceptable salts thereof, where Q is a five-, or six-, or seven-membered heterocyclic ring containing 1, 2, 3 or 4 members of the heteroatomic ring selected from N, O and S, where said heterocyclic ring is optionally substituted with one, two or three substituents, which may be identical or different and are selected from (L)-R¹⁰, where L is a bond or a CH₂ group and R¹⁰ is independently selected from hydrogen, fluorine, chlorine, bromine, cyano, oxo, hydroxy, OR¹⁵, NR¹⁵R¹⁶, COR¹⁵, CSR¹⁵, COOR¹⁵, COSR¹⁵, CONR¹⁵R¹⁶, CSNR¹⁵R¹⁶, SR¹⁵, SOR¹⁵, SO₂R¹⁵, C_1-6alkyl, C_3-6cycloalkyl, C_4-6cycloalkylalkyl, C_4-6alkylcycloalkyl or C_5-6alkylcycloalkylalkyl group which is optionally substituted with one to six fluorine atoms and in which one or two, but not all, carbon atoms can be optionally substituted by a heteroatom selected from O, N and S; and a 5- or 6-membered aryl or heteroaryl group containing 0, 1, 2, 3 or 4 heteroatoms selected from O, N and S, which is optionally substituted with C_1-6alkyl, C_3-6cycloalkyl, C_4-6cycloalkylalkyl, C_4-6alkylcycloalkyl or C_5-6alkylcycloalkylalkyl group; where R¹⁵ and R¹⁶ are identical or different or may be linked together to form a ring and each is independently selected from hydrogen, C_1-6alkyl, C_3-6cycloalkyl, C_4-6cycloalkylalkyl, C_4-6alkylcycloalkyl or C_5-6alkylcycloalkyl group, which is optionally substituted with 1 to 3 fluorine atoms and in which one or two, but not all, of the carbon atoms can be optionally substituted with a heteroatom selected from O, N, and S; or groups of formula -CH₂CH₂NHC(O)OCH₂-phenyl; or a 5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl group; or groups of formula (L)-R¹⁸, where L is a bond or a CH₂ group or CH₂CH₂ and R¹⁸ represents a 5- or 6-membered ring containing 0, 1, 2 or 3 heteroatoms selected from O, N and S, which is optionally substituted with one or two fluorine, chlorine or bromine atoms; R³ selected from hydrogen, cyano, hydroxy, amino and C_1-9alkyl, C_3-9cycloalkyl, C_4-9cycloalkylalkyl, C_4-9alkylcycloalkyl or C_5-9alkylcycloalkylalkyl group in which one carbon atom may be optionally replaced with O; and R⁴ is hydrogen or C_1-6alkyl, C_3-6cycloalkyl, C_4-6cycloalkylalkyl, C_4-6alkylcycloalkyl or C_5-6alkylcycloalkylalkyl group which is optionally substituted by one fluorine atom, which are agonists of the muscarinic M1 receptor and/or M4 receptor.

EFFECT: compounds are suitable for the treatment of muscarinic M1/M4 receptor mediated diseases.

19 cl, 2 dwg, 4 tbl